Cyber Threat Report

Penetration Testing for Your Organization: The Ins and Outs

By 2025, cybercrime will cost the world an estimated $10.5 trillion annually. As internet use grows, so does the threat of cyberattacks. For organizations, such attacks can result in devastating losses. As such, you want to make sure that you're always taking the proper measures to reduce the risk of your organization falling victim to hackers.

There are various methods of increasing cybersecurity. One of them is through the use of penetration testing. It's important to know what this is, and when to do it.

Want to know when you should perform a penetration test? keep reading to find out more.

pen testingWhat Is Penetration Testing?

A penetration test (or pen test) is a deliberate form of authorized hacking that your organization can use to test its own cybersecurity. It involves hiring an outside expert to probe applications and networks to test for vulnerabilities and weaknesses.

If they find anything that a hacker could potentially exploit, they will put it in a report and notify you at which time you can take action to mitigate the risk. This will help keep your infrastructure and your stakeholders safe.

How Does Penetration Testing Work?

When you hire a pen tester, they act as a typical hacker would. Using advanced techniques, they can find gaps in your security that most people would never notice. including:

  • Sending phishing emails to your employees (a.k.a Social Engineer)
  • Exploiting system configurations
  • Probing web-based applications

Sometimes testers will perform longer operations, observing and analyzing your organization over a number of hours or even days. This way, they may be able to determine certain behaviors or patterns that present vulnerabilities.

Another example of a Social Engineering test would be to leave  USB thumb drives in a public area. If an employee inserts into their computer, a small file is written to the computer that alerts the tester which machine was compromised. The proper response would be additional security awareness training for the employee so that they are more aware of the types of risks they might face.

Are Penetration Tests Necessary?

Annual pen tests are mandated in certain sectors including financial, energy, and health care. To stay compliant with ISO 27001 and others, you'll need to conduct regular pen tests. Any way you look at it, it's still considered industry best practice for maintaining a high level of cybersecurity.

Benefits of Penetration Testing

Identify Vulnerabilities

Cybercriminals are always looking for new ways to carry out attacks and find new exploits. When hackers discover these, they can employ things like SQL injections, malware, ransomware, and other attack vectors to steal data and harm your business.

A system that appears to be secure now may have vulnerabilities tomorrow, next week, or next month.  Security is an ongoing process and new vulnerabilities that might affect your enterprise appear daily. With regular pen testing, you'll be made aware of vulnerabilities hopefully before a hacker strikes and causes you harm. 

Specify High-Risk Weaknesses That Result From Smaller Vulnerabilities

There may be multiple vulnerabilities in your system which are somewhat lower in risk on their own. A skilled Hacker may be able to take advantage of these, however, to create intrusion sequences. This can allow them to combine low-risk vulnerabilities into a larger problem.

While automated systems are a good first-line defense, they don’t replace humans. Automated security systems can sometimes overlook vulnerabilities that seem insignificant. Pen testers, however, will look more thoroughly and be able to determine if these seemingly unimportant issues could actually present a threat.

Generate Reports to Provide Specific Advice

After conducting a pen test, the tester will provide you with a report of their findings. This report will highlight what risks there are, and their severity, and if it is a top-quality report, it will also explain what has to be done to mitigate the risk. A good report will also list the risks in order of severity – Low, medium, High, and Severe or Critical.

Generic software can also provide reports, but they're not comprehensive. They may give generic tips on resolving issues,  and often contain false positives that say there is a problem when in fact there isn’t.

When Should You a Conduct Penetration Test?

While pen tests are important, you shouldn't start one too early. This mistake is fairly common, as businesses want to know if their new network is secure as quickly as possible. The issue is that new networks and systems go through a lot of changes early on, and a pen test won't be effective until right before they are production ready. 

The best time to start testing a new environment is as soon as no more changes are being made to a system, and just before it's put into production.

Organizations often try to test early to maximize the ROI (return on investment) and this can result in services going live without proper testing with hackers taking full advantage of this.

How Often Should You Conduct a Penetration Test?

Certain variables might make it ideal to test more or less frequently, such as:

Regulations and Compliance

Different industries have various regulations regarding pen testing and other security tasks. You'll need to ensure you're following the correct compliance for your business's industry.

Company Size

In general, a larger company will have a larger online presence. This also means there will be a greater risk of attack from hackers. As such, more frequent testing is recommended.


Pen tests come at a cost and you will get what you pay for, so a smaller budget might limit how much testing you can do. If you have a larger budget, you'll be able to test more thoroughly and more often.

The bottom line is that Penetration Testing should be done at least once a year, if not twice. 


A penetration test can help ensure your infrastructure and computing systems are not open to outside attackers and meet the regulatory requirements mandated by your organization.

At JANUS Associates, our mission is to improve the information security of our clients, and society at large. In business since 1988, JANUS offers a full range of high-quality cyber security, privacy, and regulatory compliance services at affordable costs.

We understand the challenges that organizations of all sizes face. We can help you achieve your information security goals regardless of your size. To learn more about how a team of affordable professionals can help you secure your organization, contact our Corporate Director, Chris Kniffin.